The Synthesis and Characterization of Oxetane for the Cationic Curing Monomer

doi:10.7517/issn.1674-0475.190405

Imaging Science and Photochemistry ›› 2019, Vol. 37 ›› Issue (4): 297-303.DOI: 10.7517/issn.1674-0475.190405

• Review and Articles • Previous Articles Next Articles

The Synthesis and Characterization of Oxetane for the Cationic Curing Monomer

DING Lili¹, HUANG Shixiang¹, BAO Yang¹, JIAO Hongjun², LIU Xinfang², LIU Anchang¹

1. School of Chenmical Engineering and Pharmacy, Wuhan Institute Of Technology, Wuhan 430074, Hubei, P. R. China;
2. Hubei Gurun Technology Corporation, Jingmen 448000, Hubei, P. R. China

Received:2019-04-12 Online:2019-07-15 Published:2019-07-15

Abstract

Abstract: 3-Ethyl-3-methanesulfonylmethyloxetane, which was prepared from the reaction of 3-ethyl-3-hydroxymethyloxetane with methylsulfonyl chloride, reacted with ethylene glycol under alkaline conditions and PEG600 as a phase transfer catalyst to give 2-[(3-ethyl-3-oxetanyl)methoxy]ethanol. Then 2-[(3-ethyl-3-oxetanyl)methoxy]ethanol reacted with methyl methacrylate to give the target compound of 2-[(3-ethyl-3-oxetanyl)methoxy]ethyl methacrylate. 3-Ethyl-3-[(2-propen-1-yloxy)methyl]oxetane, which was prepared by the reaction of 3-ethyl-3-hydroxymethyloxetane with 3-bromopropene reacted with triethoxysilane under catalysis of chloroplatinic acid to give 3-ethyl-3-[3-(triethoxysilyl)propoxy]methyl]oxetane. The structure of title compounds were identified by IR and ¹HNMR spectrum.

Key words: 2-[(3-ethyl-3-oxetanyl)methoxy]ethyl methacrylate, 3-ethyl-3-[3-(triethoxysilyl)propoxy]me-thyl]oxetane, cationic curing

DING Lili, HUANG Shixiang, BAO Yang, JIAO Hongjun, LIU Xinfang, LIU Anchang. The Synthesis and Characterization of Oxetane for the Cationic Curing Monomer[J]. Imaging Science and Photochemistry, 2019, 37(4): 297-303.

References

[1] 张娜,陈媛,聂俊,杨金梁. 光固化阳离子活性稀释剂研究进展[J]. 影像科学与光化学,2016,34(6):491-504. Zhang N, Chen Y, Nie J, Yang J L. Research progress of cationic reactive diluents for photopolymerization[J].Imaging Science and Photochemistry, 2016, 34(6):491-504.
[2] 苏建宇,汪鲁焱,郑怡倩,刘敏,卜凡乐,刘安昌. 新型阳离子光固化活性单体3,3-[氧基双亚甲基]-双[3-甲基]氧杂环丁烷的合成[J]. 武汉工程大学学报, 2018, 40(3):263-266. Su J Y, Wang L Y, Zheng Y Q, Liu M, Bu F L, Liu A C. Synthesis of bis(3-methyloxetan-3-yl)methyl ether for novel cationic photocuringmonomer[J]. Journal of Wuhan Institute of Technology, 2018, 40(3):263-266.
[3] Crivello J V. Investigations of the reactivity of "kick-started" oxetanes in photoinitiated cationic polymerization[J]. Journal of Polymer Science Part A Polymer Chemistry, 2015, 53(4):586-593.
[4] Qian X C. Preparation of oxetan containing ester compounds[P]. WO2016066146, 2016-05-06.
[5] El-Ghayoury A, Boukaftane C, De Ruiter B, Van Der Linde R. Ultraviolet-ultraviolet dual-cure process based on acrylate oxetane monomers[J]. Journal of Polymer Science, Part A:Polymer Chemistry, 2003, 41(4):469-475.
[6] Suzuki H, Goto K, Washimi A. Preparation of silylpro-poxyoxetanes for cationically photocurable polymer compositions[P]. JP2000247981, 2000-9-12.
[7] Schulte B, Dannenberg C A, Keul H, Moeller M. Formation of linear and cyclic polyoxetanes in the cationic ring-opening polymerization of 3-allyloxymethyl-3-ethyloxetane and subsequent postpolymerization modification of poly(3-allyloxymethyl-3-ethyloxetane)[J]. Journal of Polymer Science, Part A:Polymer Chemistry, 2013, 51(5):1243-1254.
[8] Yeong C H, Su L J. Photosensitive resin composition with good adhesion[P]. KR2015081581, 2015-01-15.

The Synthesis and Characterization of Oxetane for the Cationic Curing Monomer

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 0

Recommended Articles

Metrics

Comments